Poly(vinylbenzyl alcohol) can be used in several applications, for example as an adhesive in bonding non-adhering layers, in photoresist formulations and as an undercoat layer in imaging members.
Several attempts have been made to synthesize poly(vinylbenzyl alcohol). One synthesis method is described in U.S. Pat. No. 3,879,328. According to the method, poly(vinylbenzyl alcohol) is formed by the polymerization of vinylbenzyl alcohol which is prepared from the hydrolysis of vinylbenzyl chloride. One drawback of the method may be that the overall yield is low at about 5%, due primarily to the low yield of formation of vinyl benzyl alcohol from vinyl benzyl chloride. Other disadvantages may include the difficulty in separating vinylbenzyl chloride as a starting material from vinylbenzyl alcohol and vinylbenzyl ether, and the formation of residual divinylbenzyl ether which may lead to the crosslinking of poly(vinylbenzyl alcohol) and gel formation.
According to the method of U.S. Pat. No. 6,200,716, poly(vinylbenzyl alcohol) and poly(vinylbenzyl alcohol-vinylbenzyl acetate) can be formed by the borane reduction of poly(vinylbenzyl acetate) which itself was formed by the reaction of poly(vinylbenzyl chloride) with sodium acetate. Poly(vinylbenzyl acetate) is hydrolyzed or reduced to form poly(vinylbenzyl alcohol). Partial reduction of the acetate produces copolymers of the poly(vinylbenzyl alcohol-vinylbenzyl acetate). Although borane reduction affords control of macromolecular structure, a drawback of the method may be that the yield is low. Another drawback is that borane is difficult to handle, and the process is expensive and difficult to scale up.
It is therefore desirable to provide a process for the preparation of poly(vinylbenzyl alcohol) using readily available reagents which may not require any special handling. Furthermore, it is desirable to provide a process for the preparation of poly(vinylbenzyl alcohol) in high purity of at least about 90%. The process is amenable to scale-up without the production of environmentally harmful by-products.